Benzoic Acid → Oxindole

HRID 1645259Notes

Reaction equation

HRID 1645259 reaction equation
[C:1](O)(=[O:8])[C:2]1C=CC=CC=1.[CH:10]1[CH:11]=[CH:12][C:13]2N(O)N=[N:16][C:14]=2[CH:15]=1.CCN=C=NCCCN(C)C.CN1CCCNCC1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[NH:16]1[C:14]2[C:13](=[CH:12][CH:11]=[CH:10][CH:15]=2)[CH2:2][C:1]1=[O:8]

Participants

8

Reactant 5

HCID 243Benzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2283491-Methylhomopiperazine

Product 1

HCID 321710Oxindole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-3-(5-chloro-2-oxoindolin-3-ylidene)methyl)furan-2-yl)benzoic acid (541 mg, 1.48 mmol) and HOBt (400 mg, 2.96 mmol) in DMF (2 mL) was added EDCI (565 mg, 2.96 mmol). The reaction was stirred at rt for 10 min and then added 1-methyl homopiperazine (0.734 mL, 5.92 mmol) followed by DIEA (1 mL). The reaction mixture was stirred at rt for 1 h and diluted with H2O (10 mL). The mixture was extracted with EtOAc, dried over Na2SO4 and concentrated. The crude was purified by preparative TLC eluting with 2% methanol in dichloromethane to give (E)-5-chloro-3-(5-(3-(4-methyl-1,4-diazepane-1-carbonyl)phenyl)furan-2-yl)methylene)indolin-2-one. LCMS (ES): m/z 462 [M+1]+.

Workup

  1. stirringThe reaction mixture was stirred at rt for 1 h
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude was purified by preparative TLC
  6. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-51fb5ca64f254733be23bbf854112179
Source dataset
uspto-grants-2012_02
Patent number
US08124649B2

Reaction notes

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